GB1195628A - Aroyl-Substituted Pyrroles - Google Patents
Aroyl-Substituted PyrrolesInfo
- Publication number
- GB1195628A GB1195628A GB3527768A GB3527768A GB1195628A GB 1195628 A GB1195628 A GB 1195628A GB 3527768 A GB3527768 A GB 3527768A GB 3527768 A GB3527768 A GB 3527768A GB 1195628 A GB1195628 A GB 1195628A
- Authority
- GB
- United Kingdom
- Prior art keywords
- lower alkyl
- pyrrole
- formula
- acid
- cooh
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/33—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/337—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Abstract
1,195,628. Substituted pyrroles; oximes; acid chlorides. McNEIL LABORATORIES Inc. 24 July, 1968 [26 July, 1967; 1 July, 1968], No. 35277/68. Heading C2C. Novel 5-aroyl-pyrrole derivatives of the formulµ Ia, Ib, Ic and Id and the therapeutically acceptable basic salts of the acis thereof, wherein: Ar represents a phenyl, monosubstituted phenyl or polysubstituted phenyl group, each substituent being a halogen, lower alkyl, lower alkoxy, nitro, amino, methylthio or cyano group; Ar 1 represents a phenyl, monosubstituted phenyl or polysubstituted phenyl group, each substituent being a halogen, lower alkyl or lower alkoxy group; R represents a hydrogen or lower alkyl group; R 1 represents a hydrogen, lower alkyl or benzyl group; R 2 represents a CN, COOH, COO-(lower alkyl), CONH 2 , CONH (lower alkyl) or CON (lower alkyl) 2 group; and R 3 represents a COOH, COO-(lower alkyl), CONH 2 , CONH (lower alkyl) or CON (lower alkyl) 2 group; provided that: (i) when Ar is nitrophenyl or aminophenyl, then R is hydrogen, R 1 is lower alkyl and R 2 is CN 1 , COOH or COO-(lower alkyl); (ii) when Ar is cyanophenyl or methylthiophenyl, then R 1 is lower alkyl and R 2 is COOH or COO-(lower alkyl) ; and (iii) when R 1 is hydrogen, R is hydrogen, are prepared by (a) reacting a compound of the Formula II with a compound of the formula in the presence of a Lewis acid and a solvent, wherein R<SP>1</SP> is cyano or lower alkoxycarbonyl, whereafter the product may be converted to the corresponding carboxylic acid by hydrolysis, and in the instance of compounds of the Formula (Ia) wherein R is lower alkyl and R 2 is -CN, COOH or COO-(lower alkyl), C- alkylating a compound of the formula wherein R<SP>11</SP> is lower alkyl or benzyl and Ar<SP>1</SP> is phenyl or phenyl substituted with halogen, lower alkyl, lower alkoxy or cyano, with a lower alkyl halide in the presence of a strong base, the product may then be hydrolysed to the free acid; and in the instance wherein it is desired to obtain compounds wherein R 1 is lower alkyl, Ar is the same as Ar<SP>1</SP>, R is lower alkyl and R 2 is CN or COOH, N-alkylating a compound of the formula followed by C-alkylation of the product, if desired, followed by hydrolysis to the corresponding free acid; and in the instance wherein Ar is nitrophenyl, and R 2 is equal to R<SP>1</SP>, the nitro function may be catalytically hydrogenated to yield the corresponding aminophenyl product, if desired, followed by hydrolysis to the corresponding free acid; when R 2 is COOH esterification with a lower alkanol yields the corresponding esters, and when R 2 is CN partial hydrolysis gives the corresponding amides; conversion of the COOH group to an acid chloride followed by reaction with a lower alkyl amine (mono- or di-alkyl) yields the corresponding amides; or (b) reacting a compound of the Formula II above, wherein Ar is other than aminophenyl, with a compound of the formula in the presence of a Lewis acid and a solvent, hydrolysis yields the free acid of Formula (Ib), catalytic hydrogenation of the nitrophenyl will give the corresponding aminophenyl, if desired, followed by hydrolysis of the ester function to give the free acid; the free acids of Formula (Ib) may be converted to their amides with ammonia or a lower (mono- or di-) alkyl amine; (c) and (d) decarboxylating a compound of the formulµ by heating in a basic organic solvent to give compounds XVI and XXIII of the respective formulµ hydrolysis of (XVI) will give the free acid, (XXIII) may be esterified with a lower alkanol, the compounds may be converted to their amides by treatment of the acid with ammonia or a lower (mono- or di-) alkyl amine; and, if desired, preparing therapeutically acceptable salts of acids prepared by the above processes by treatment with an appropriate base. The pyrrole-2-acetate starting materials may be prepared by the action of diazomethane on the acid. The pyrrole-2-propionates may be prepared from the pyrrole-2-aldehydes and ethoxycarbonyl methylene triphenylphosphorane, followed by hydrogenation of the resulting pyrrole-2-acrylates. The aroyl chloride starting materials may be obtained by the action of thionyl chloride on the corresponding acids. The pyrrole-2-acetonitriles may be formed from corresponding pyrrole, dimethylamine and formalin, followed by the addition of methyl iodide to the resulting 2-dimethylaminomethyl-1-benzyl-pyrrole to form the corresponding quaternary salt and then treatment with sodium cyanide. 1-Aryl- 1,2,3 - butanetrione - 2 - oximes may be prepared by treating the 1-aryl-1,3-butanedione with nitrous acid, cyclization of the oxime with diethyl acetone dicarboxylate gives the ethyl- 5 - aroyl - 3 - ethoxy - carbonyl - 4 - methyl pyrrole-2-acetate which upon hydrolysis yields the corresponding acids, treatment with ethanolic hydrogen chloride gives the ethyl 5-aroyl-3- carboxy - 4 - methyl - pyrrole - 2 - acetate. The ethyl 5 - aroyl - 2,4 - dimethyl pyrrole - 3 - acetates are prepared from ethyl 2,4-dimethyl-pyrrole-3- acetates and an aroyl chloride, treatment with sulphuryl chloride yields the ethyl-5-aroyl-4- methyl - 2 - trichloromethyl - pyrazole - 3 - acetates, refluxing with water in dioxan gives the corresponding 3-acetic acids. Methyl pyrrole-2- acetate and methyl 1-methyl-pyrrole-2-acetate by esterifying required acids with diazomethane. Ethyl 2 - (1 - methyl - 2 - pyrrolyl) - propionate is prepared by hydrogenating the corresponding acrylate. Pharmaceutical compositions contain the compounds Ia, Ib, Ic and Id above and a carrier. The compositions have anti-inflammatory activity and may be administered orally.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US65607467A | 1967-07-26 | 1967-07-26 | |
US74134868A | 1968-07-01 | 1968-07-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1195628A true GB1195628A (en) | 1970-06-17 |
Family
ID=27097103
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3527768A Expired GB1195628A (en) | 1967-07-26 | 1968-07-24 | Aroyl-Substituted Pyrroles |
Country Status (10)
Country | Link |
---|---|
AT (1) | AT289096B (en) |
BE (1) | BE718594A (en) |
CH (1) | CH518929A (en) |
DK (1) | DK136059B (en) |
ES (1) | ES356485A1 (en) |
FR (1) | FR1574570A (en) |
GB (1) | GB1195628A (en) |
IL (1) | IL30426A (en) |
NL (1) | NL162638C (en) |
SE (1) | SE338993B (en) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1983001774A1 (en) * | 1981-11-23 | 1983-05-26 | Riker Laboratories Inc | Substituted pyrrole |
US4396626A (en) | 1980-10-09 | 1983-08-02 | Beecham Group Limited | Cyclic compounds and their use |
FR2522324A1 (en) * | 1982-02-26 | 1983-09-02 | Sigma Tau Ind Farmaceuti | PYRROLE ACETAMIDES, PROCESS FOR THEIR PREPARATION AND THERAPEUTIC COMPOSITION CONTAINING SAME |
EP0115424A1 (en) * | 1983-01-26 | 1984-08-08 | McNeilab, Inc. | Pyrrole-2-acetylamino acid derivatives |
WO1996010013A1 (en) * | 1994-09-27 | 1996-04-04 | Ono Pharmaceutical Co., Ltd. | Five membered heterocyclic compounds |
US5859042A (en) * | 1995-09-27 | 1999-01-12 | Ono Pharmaceutical Co., Ltd. | Five membered heterocyclic compounds |
US7544711B2 (en) | 1996-09-04 | 2009-06-09 | Nicox S.A. | Use of nitroderivatives in urinary incontinence |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2128205B1 (en) * | 1971-03-11 | 1974-05-24 | Roussel Uclaf | |
FR2068425B1 (en) * | 1969-11-12 | 1973-01-12 | Roussel Uclaf | |
US3752826A (en) * | 1970-01-26 | 1973-08-14 | Mcneilab Inc | Aroyl substituted pyrroles |
DE3026402A1 (en) * | 1980-07-11 | 1982-02-04 | Syntex Corp., Palo Alto, Calif. | Non-steroidal antiinflammatory agents - for treatment of micro:vascular disease, e.g. diabetic retinopathy or diabetic nephropathy |
IT1308633B1 (en) | 1999-03-02 | 2002-01-09 | Nicox Sa | NITROSSIDERIVATI. |
JP5208411B2 (en) | 2003-02-06 | 2013-06-12 | ドムペ・ファ.ル.マ・ソチエタ・ペル・アツィオーニ | 2-Aryl-acetic acid, derivatives thereof, and pharmaceutical compositions containing them |
-
1968
- 1968-07-24 GB GB3527768A patent/GB1195628A/en not_active Expired
- 1968-07-24 SE SE1007068A patent/SE338993B/xx unknown
- 1968-07-24 ES ES356485A patent/ES356485A1/en not_active Expired
- 1968-07-25 CH CH1116368A patent/CH518929A/en not_active IP Right Cessation
- 1968-07-25 IL IL3042668A patent/IL30426A/en unknown
- 1968-07-25 FR FR1574570D patent/FR1574570A/fr not_active Expired
- 1968-07-25 BE BE718594D patent/BE718594A/xx not_active IP Right Cessation
- 1968-07-26 DK DK361168A patent/DK136059B/en not_active IP Right Cessation
- 1968-07-26 NL NL6810664A patent/NL162638C/en not_active IP Right Cessation
- 1968-07-26 AT AT730768A patent/AT289096B/en not_active IP Right Cessation
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4396626A (en) | 1980-10-09 | 1983-08-02 | Beecham Group Limited | Cyclic compounds and their use |
WO1983001774A1 (en) * | 1981-11-23 | 1983-05-26 | Riker Laboratories Inc | Substituted pyrrole |
US4418074A (en) | 1981-11-23 | 1983-11-29 | Riker Laboratories, Inc. | 2,6 Di(t-butyl)-4-(2'-pyrrol)-phenol and anti-inflammatory use thereof |
FR2522324A1 (en) * | 1982-02-26 | 1983-09-02 | Sigma Tau Ind Farmaceuti | PYRROLE ACETAMIDES, PROCESS FOR THEIR PREPARATION AND THERAPEUTIC COMPOSITION CONTAINING SAME |
EP0115424A1 (en) * | 1983-01-26 | 1984-08-08 | McNeilab, Inc. | Pyrrole-2-acetylamino acid derivatives |
WO1996010013A1 (en) * | 1994-09-27 | 1996-04-04 | Ono Pharmaceutical Co., Ltd. | Five membered heterocyclic compounds |
US5859042A (en) * | 1995-09-27 | 1999-01-12 | Ono Pharmaceutical Co., Ltd. | Five membered heterocyclic compounds |
US7544711B2 (en) | 1996-09-04 | 2009-06-09 | Nicox S.A. | Use of nitroderivatives in urinary incontinence |
Also Published As
Publication number | Publication date |
---|---|
NL162638B (en) | 1980-01-15 |
IL30426A (en) | 1972-02-29 |
DK136059C (en) | 1978-01-09 |
SE338993B (en) | 1971-09-27 |
AT289096B (en) | 1971-04-13 |
NL162638C (en) | 1980-06-16 |
CH518929A (en) | 1972-02-15 |
NL6810664A (en) | 1969-01-28 |
DE1770984B2 (en) | 1975-05-22 |
FR1574570A (en) | 1969-07-11 |
DK136059B (en) | 1977-08-08 |
ES356485A1 (en) | 1970-01-16 |
DE1770984A1 (en) | 1972-04-06 |
BE718594A (en) | 1969-01-27 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed | ||
PE20 | Patent expired after termination of 20 years |